#------------------------------------------------------------------------------
#$Date: 2025-08-20 21:19:29 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301836 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/20/4302015.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4302015
loop_
_publ_author_name
'Edward C. Weintrob'
'Daniel Tofan'
'John E. Bercaw'
_publ_contact_author
;       Michael W. Day
        Beckman Institute
        California Institute of Technology
        Pasadena, CA  91125
        USA
;
_publ_contact_author_email       mikeday@caltech.edu
_publ_contact_author_fax         '(818) 449 4159'
_publ_contact_author_phone       '(818) 395 2734'
_publ_section_title
;
Synthesis and Characterization of Iron Derivatives Having a Pyridine-Linked
Bis(anilide) Pincer Ligand
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              3808
_journal_page_last               3813
_journal_paper_doi               10.1021/ic900083s
_journal_volume                  48
_journal_year                    2009
_chemical_formula_moiety         'C35 H35 N3'
_chemical_formula_sum            'C35 H35 N3'
_chemical_formula_weight         497.66
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.803(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1774(12)
_cell_length_b                   8.3901(8)
_cell_length_c                   27.039(3)
_cell_measurement_reflns_used    8568
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.95
_cell_measurement_theta_min      2.54
_cell_volume                     2756.5(5)
_computing_cell_refinement       'Bruker SAINT v6.45A'
_computing_data_collection       'Bruker SMART v5.630'
_computing_data_reduction        'Bruker SAINT v6.45A'
_computing_molecular_graphics    'Bruker XP v5.1'
_computing_publication_material  'Bruker XCIF v6.12'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.932
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       'ω scans at 5 φ settings'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0831
_diffrn_reflns_av_sigmaI/netI    0.0649
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            34841
_diffrn_reflns_theta_full        28.41
_diffrn_reflns_theta_max         28.41
_diffrn_reflns_theta_min         1.51
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.9937
_exptl_absorpt_correction_T_min  0.9732
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Blade
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.579
_refine_ls_hydrogen_treatment    Riding
_refine_ls_matrix_type           'Full matrix'
_refine_ls_number_parameters     349
_refine_ls_number_reflns         6474
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.579
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0554
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     w=1/s²(Fo²)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0939
_reflns_number_gt                4122
_reflns_number_total             6474
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic900083s_si_002_1.cif
_cod_data_source_block           '[2]H2'
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_weighting_scheme' value 'Sigma' changed to
'sigma' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'Direct methods' was changed to
'direct'.

'_atom_sites_solution_secondary' value 'Difference Fourier map' was
changed to 'difmap'.

'_atom_sites_solution_hydrogens' value 'Geometric positions' was
changed to 'geom'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4302015
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.10382(12) 0.39885(17) 0.13108(5) 0.0393(4) Uani 1 1 d . . .
H1 H 0.1060 0.4191 0.1631 0.047 Uiso 1 1 calc R . .
N2 N 0.37310(10) 0.51579(15) 0.18558(5) 0.0214(3) Uani 1 1 d . . .
N3 N 0.49041(10) 0.24250(15) 0.17586(4) 0.0235(3) Uani 1 1 d . . .
H3 H 0.4280 0.2916 0.1677 0.028 Uiso 1 1 calc R . .
C1 C 0.15694(13) 0.5009(2) 0.09975(6) 0.0271(4) Uani 1 1 d . . .
C2 C 0.12648(14) 0.5049(2) 0.04930(6) 0.0334(5) Uani 1 1 d . . .
H2 H 0.0682 0.4388 0.0362 0.040 Uiso 1 1 calc R . .
C3 C 0.17978(14) 0.6037(2) 0.01812(6) 0.0340(4) Uani 1 1 d . . .
H3A H 0.1584 0.6051 -0.0163 0.041 Uiso 1 1 calc R . .
C4 C 0.26387(14) 0.7005(2) 0.03655(6) 0.0356(5) Uani 1 1 d . . .
H4 H 0.3002 0.7694 0.0151 0.043 Uiso 1 1 calc R . .
C5 C 0.29518(13) 0.6967(2) 0.08663(6) 0.0306(4) Uani 1 1 d . . .
H5 H 0.3535 0.7635 0.0993 0.037 Uiso 1 1 calc R . .
C6 C 0.24339(12) 0.59782(19) 0.11864(6) 0.0221(4) Uani 1 1 d . . .
C7 C 0.27810(13) 0.59336(18) 0.17273(6) 0.0221(4) Uani 1 1 d . . .
C8 C 0.21594(13) 0.6639(2) 0.20733(6) 0.0269(4) Uani 1 1 d . . .
H8 H 0.1502 0.7192 0.1972 0.032 Uiso 1 1 calc R . .
C9 C 0.25035(13) 0.65336(19) 0.25699(6) 0.0277(4) Uani 1 1 d . . .
H9 H 0.2085 0.7012 0.2814 0.033 Uiso 1 1 calc R . .
C10 C 0.34616(13) 0.57258(19) 0.27050(6) 0.0245(4) Uani 1 1 d . . .
H10 H 0.3703 0.5625 0.3045 0.029 Uiso 1 1 calc R . .
C11 C 0.40758(12) 0.50570(18) 0.23401(5) 0.0205(4) Uani 1 1 d . . .
C12 C 0.51219(12) 0.42023(18) 0.24690(5) 0.0204(4) Uani 1 1 d . . .
C13 C 0.57468(13) 0.46259(19) 0.29031(6) 0.0253(4) Uani 1 1 d . . .
H13 H 0.5492 0.5464 0.3102 0.030 Uiso 1 1 calc R . .
C14 C 0.67179(13) 0.3870(2) 0.30520(6) 0.0295(4) Uani 1 1 d . . .
H14 H 0.7117 0.4168 0.3352 0.035 Uiso 1 1 calc R . .
C15 C 0.71025(13) 0.2667(2) 0.27578(6) 0.0285(4) Uani 1 1 d . . .
H15 H 0.7776 0.2146 0.2854 0.034 Uiso 1 1 calc R . .
C16 C 0.65160(12) 0.22199(19) 0.23274(6) 0.0259(4) Uani 1 1 d . . .
H16 H 0.6796 0.1403 0.2128 0.031 Uiso 1 1 calc R . .
C17 C 0.55170(12) 0.29459(19) 0.21798(6) 0.0216(4) Uani 1 1 d . . .
C18 C 0.04583(15) 0.2616(2) 0.11188(6) 0.0312(4) Uani 1 1 d . . .
C19 C -0.06848(15) 0.2578(2) 0.11053(6) 0.0314(4) Uani 1 1 d . . .
C20 C -0.12158(15) 0.1243(2) 0.09032(6) 0.0337(5) Uani 1 1 d . . .
H20 H -0.1997 0.1207 0.0889 0.040 Uiso 1 1 calc R . .
C21 C -0.06524(15) -0.0034(2) 0.07219(6) 0.0330(4) Uani 1 1 d . . .
C22 C 0.04851(14) 0.0030(2) 0.07439(6) 0.0364(5) Uani 1 1 d . . .
H22 H 0.0884 -0.0846 0.0624 0.044 Uiso 1 1 calc R . .
C23 C 0.10586(14) 0.1350(2) 0.09376(6) 0.0338(5) Uani 1 1 d . . .
C24 C -0.13282(16) 0.3938(2) 0.13115(7) 0.0451(5) Uani 1 1 d . . .
H24A H -0.2115 0.3779 0.1227 0.068 Uiso 1 1 calc R . .
H24B H -0.1092 0.4945 0.1169 0.068 Uiso 1 1 calc R . .
H24C H -0.1194 0.3972 0.1673 0.068 Uiso 1 1 calc R . .
C25 C -0.12502(16) -0.1478(2) 0.05115(7) 0.0489(6) Uani 1 1 d . . .
H25A H -0.1569 -0.2069 0.0780 0.073 Uiso 1 1 calc R . .
H25B H -0.0732 -0.2164 0.0349 0.073 Uiso 1 1 calc R . .
H25C H -0.1838 -0.1139 0.0269 0.073 Uiso 1 1 calc R . .
C26 C 0.23003(14) 0.1393(2) 0.09484(7) 0.0446(5) Uani 1 1 d . . .
H26A H 0.2577 0.0336 0.0866 0.067 Uiso 1 1 calc R . .
H26B H 0.2599 0.1697 0.1280 0.067 Uiso 1 1 calc R . .
H26C H 0.2531 0.2172 0.0706 0.067 Uiso 1 1 calc R . .
C27 C 0.52182(12) 0.11546(19) 0.14516(6) 0.0223(4) Uani 1 1 d . . .
C28 C 0.52639(12) -0.0416(2) 0.16263(6) 0.0248(4) Uani 1 1 d . . .
C29 C 0.55389(12) -0.1613(2) 0.13016(6) 0.0267(4) Uani 1 1 d . . .
H29 H 0.5593 -0.2678 0.1420 0.032 Uiso 1 1 calc R . .
C30 C 0.57367(13) -0.1313(2) 0.08117(6) 0.0275(4) Uani 1 1 d . . .
C31 C 0.56733(13) 0.0251(2) 0.06487(6) 0.0302(4) Uani 1 1 d . . .
H31 H 0.5799 0.0479 0.0313 0.036 Uiso 1 1 calc R . .
C32 C 0.54301(12) 0.15028(19) 0.09630(6) 0.0251(4) Uani 1 1 d . . .
C33 C 0.49737(14) -0.0839(2) 0.21426(6) 0.0337(4) Uani 1 1 d . . .
H33A H 0.4832 -0.1986 0.2162 0.050 Uiso 1 1 calc R . .
H33B H 0.4314 -0.0250 0.2223 0.050 Uiso 1 1 calc R . .
H33C H 0.5587 -0.0556 0.2379 0.050 Uiso 1 1 calc R . .
C34 C 0.59553(14) -0.2667(2) 0.04642(6) 0.0369(5) Uani 1 1 d . . .
H34A H 0.6566 -0.3316 0.0607 0.055 Uiso 1 1 calc R . .
H34B H 0.6148 -0.2236 0.0144 0.055 Uiso 1 1 calc R . .
H34C H 0.5294 -0.3330 0.0415 0.055 Uiso 1 1 calc R . .
C35 C 0.53908(14) 0.3205(2) 0.07839(6) 0.0341(4) Uani 1 1 d . . .
H35A H 0.4624 0.3566 0.0750 0.051 Uiso 1 1 calc R . .
H35B H 0.5713 0.3271 0.0462 0.051 Uiso 1 1 calc R . .
H35C H 0.5810 0.3883 0.1024 0.051 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C18 120.80(13) . . ?
C11 N2 C7 119.00(13) . . ?
C17 N3 C27 124.37(12) . . ?
C2 C1 N1 120.47(15) . . ?
C2 C1 C6 119.30(15) . . ?
N1 C1 C6 120.22(14) . . ?
C3 C2 C1 120.67(16) . . ?
C4 C3 C2 120.27(16) . . ?
C3 C4 C5 119.50(16) . . ?
C6 C5 C4 121.31(16) . . ?
C5 C6 C1 118.94(15) . . ?
C5 C6 C7 121.10(14) . . ?
C1 C6 C7 119.96(14) . . ?
N2 C7 C8 122.15(14) . . ?
N2 C7 C6 116.41(14) . . ?
C8 C7 C6 121.44(14) . . ?
C7 C8 C9 119.20(15) . . ?
C10 C9 C8 119.07(15) . . ?
C9 C10 C11 119.67(14) . . ?
N2 C11 C10 120.90(14) . . ?
N2 C11 C12 117.71(13) . . ?
C10 C11 C12 121.39(14) . . ?
C13 C12 C17 117.77(14) . . ?
C13 C12 C11 118.97(14) . . ?
C17 C12 C11 123.25(13) . . ?
C14 C13 C12 122.38(15) . . ?
C13 C14 C15 118.92(15) . . ?
C16 C15 C14 120.50(15) . . ?
C15 C16 C17 121.12(15) . . ?
N3 C17 C16 120.52(14) . . ?
N3 C17 C12 120.20(13) . . ?
C16 C17 C12 119.27(14) . . ?
C19 C18 C23 121.33(16) . . ?
C19 C18 N1 119.83(17) . . ?
C23 C18 N1 118.83(16) . . ?
C20 C19 C18 117.95(17) . . ?
C20 C19 C24 121.01(16) . . ?
C18 C19 C24 121.03(16) . . ?
C21 C20 C19 122.48(17) . . ?
C20 C21 C22 118.34(17) . . ?
C20 C21 C25 121.32(17) . . ?
C22 C21 C25 120.34(18) . . ?
C21 C22 C23 121.50(18) . . ?
C22 C23 C18 118.39(16) . . ?
C22 C23 C26 120.14(18) . . ?
C18 C23 C26 121.47(16) . . ?
C32 C27 C28 120.76(15) . . ?
C32 C27 N3 118.11(14) . . ?
C28 C27 N3 121.06(14) . . ?
C29 C28 C27 118.24(15) . . ?
C29 C28 C33 119.80(15) . . ?
C27 C28 C33 121.89(15) . . ?
C30 C29 C28 122.51(16) . . ?
C29 C30 C31 117.83(15) . . ?
C29 C30 C34 120.51(16) . . ?
C31 C30 C34 121.59(16) . . ?
C30 C31 C32 121.95(16) . . ?
C27 C32 C31 118.67(15) . . ?
C27 C32 C35 119.94(14) . . ?
C31 C32 C35 121.39(15) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.3935(19) . ?
N1 C18 1.430(2) . ?
N2 C11 1.3511(18) . ?
N2 C7 1.3525(18) . ?
N3 C17 1.3900(17) . ?
N3 C27 1.4191(19) . ?
C1 C2 1.390(2) . ?
C1 C6 1.400(2) . ?
C2 C3 1.376(2) . ?
C3 C4 1.374(2) . ?
C4 C5 1.383(2) . ?
C5 C6 1.381(2) . ?
C6 C7 1.496(2) . ?
C7 C8 1.376(2) . ?
C8 C9 1.383(2) . ?
C9 C10 1.378(2) . ?
C10 C11 1.395(2) . ?
C11 C12 1.483(2) . ?
C12 C13 1.4016(19) . ?
C12 C17 1.416(2) . ?
C13 C14 1.378(2) . ?
C14 C15 1.386(2) . ?
C15 C16 1.376(2) . ?
C16 C17 1.395(2) . ?
C18 C19 1.390(2) . ?
C18 C23 1.396(2) . ?
C19 C20 1.387(2) . ?
C19 C24 1.512(2) . ?
C20 C21 1.380(2) . ?
C21 C22 1.384(2) . ?
C21 C25 1.505(2) . ?
C22 C23 1.393(2) . ?
C23 C26 1.511(2) . ?
C27 C32 1.394(2) . ?
C27 C28 1.400(2) . ?
C28 C29 1.390(2) . ?
C28 C33 1.505(2) . ?
C29 C30 1.385(2) . ?
C30 C31 1.385(2) . ?
C30 C34 1.509(2) . ?
C31 C32 1.395(2) . ?
C32 C35 1.507(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 N2 0.88 2.06 2.7235(18) 130.9 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660719
2 PubChem 101463398
